1,3-Butadienylzinc trimer formed via transmetalation from 1,4-dilithio-1,3-butadienes: Synthesis, structural characterization, and application in Negishi cross-coupling

Organometallics

Volumn 31, Issue 15, 2012, Pages 5546-5550

  Zhou, Yi ^a   Zhang, Wen Xiong ^a   Xi, Zhenfeng ^a,b  

^a PEKING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

NEGISHI CROSS-COUPLING; REACTION CHEMISTRY; STRUCTURAL CHARACTERIZATION; TRANSMETALATION; X RAY STRUCTURAL ANALYSIS;

OLIGOMERS; PALLADIUM; SYNTHESIS (CHEMICAL);

BUTADIENE;

EID: 84865024534     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om3005004     Document Type: Article

References (46)

1. Knochel, P.; Almena, J.; Jones, P. Tetrahedron 1998, 54, 8275-8319
2. Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4415-4435
3. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651-2710
4. Rudolph, A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 2656-2670
5. Yu, D.; Li, B.; Shi, Z. Acc. Chem. Res. 2010, 43, 1486-1495
6. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417-1492
7. Tochtermann, W. Angew. Chem., Int. Ed. 1966, 5, 351-371
8. Uchiyama, M.; Matsumoto, Y.; Nobuto, D.; Furuyama, T.; Yamaguchi, K.; Morokuma, K. J. Am. Chem. Soc. 2006, 128, 8748-8750
9. Mulvey, R. E.; Mongin, F.; Uchiyama, M.; Kondo, Y. Angew. Chem., Int. Ed. 2007, 46, 3802-3824
10. Merkel, S.; Stern, D.; Stalke, D. Angew. Chem., Int. Ed. 2009, 48, 6350-6353
11. Clegg, W.; Conway, B.; García-Alvarez, P.; Kennedy, A. R.; Klett, J.; Mulvey, R. E.; Russo, L. Dalton Trans. 2010, 39, 62-65
12. Evans, D. F.; Maher, J. P. J. Chem. Soc. 1962, 5125-5128
13. Dessy, R. E.; Coe, G. R. J. Org. Chem. 1963, 28, 3592-3593
14. Evans, D. F.; Wharf, I. J. Organomet. Chem. 1966, 5, 108
15. Boersma, J.; Noltes, J, C. Tetrahedron Lett. 1966, 14, 1521-1525
16. Guerrero, A.; Hughes, D. L.; Bochmann, M. Organometallics 2006, 25, 1525-1527
17. Sarazin, Y.; Wright, J. A.; Harding, D. A. J.; Martin, E.; Woodman, T. J.; Hughes, D. L.; Bochmann, M. J. Organomet. Chem. 2008, 693, 1494-1501
18. MacIntosh, I. S.; Sherren, C. N.; Robertson, K. N.; Masuda, J. D.; Pye, C. C.; Clyburne, J. A. C. Organometallics 2010, 29, 2063-2068
19. Wooten, A.; Carroll, P. J.; Maestri, A. G.; Walsh, P. J. J. Am. Chem. Soc. 2006, 128, 4624-4631
20. Xi, Z. Acc. Chem. Res. 2010, 42, 1342-1351
21. Wang, C.; Yuan, J.; Li, G.; Wang, Z.; Zhang, S.; Xi, Z. J. Am. Chem. Soc. 2006, 128, 4564-4565
22. Wang, C.; Xi, Z. Chem. Commun. 2007, 5119-5133
23. Luo, Q.; Wang, C.; Zhang, W. -X.; Xi, Z. Chem. Commun. 2008, 1593-1595
24. Li, G.; Fang, H.; Li, Z.; Xi, Z. Chin. J. Chem. 2003, 21, 219-221
25. Li, G.; Fang, H.; Xi, Z. Tetrahedron Lett. 2003, 44, 8705-8708
26. Fang, H.; Zhao, C.; Li, G.; Xi, Z. Tetrahedron 2003, 59, 3779-3786
27. Dubac, J.; Laporterie, A.; Manuel, G. Chem. Rev. 1990, 90, 215-263
28. Colomer, E.; Corriu, R. J. P.; Lheureux, M. Chem. Rev. 1990, 90, 265-282
29. Gessner, V. H.; Tannacl, J. F.; Miller, A. D.; Tilley, T. D. Acc. Chem. Res. 2011, 44, 435-466
30. Massey, A. G.; Al-Jabar, N. A. A.; Humphries, R. E.; Deacon, G. B. J. Organomet. Chem. 1986, 316, 25-39
31. Humphries, R. E. Inorg. Chem. Acta 1988, 144, 163-169
32. West, A. J. Annu. Rep. Prog. Chem., Sect. A 2007, 103, 240-244
33. Balloch, L.; Garden, J. A.; Kennedy, A. R.; Mulvey, R. E.; Rantanen, T.; Robertson, S. D.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 6934-6937
34. Liu, L.; Zhang, W.-X.; Wang, C.; Wang, C. Y.; Xi, Z. Organometallics 2010, 29, 278-281
35. Luo, Q.; Wang, C.; Gu, L.; Zhang, W.-X.; Xi, Z. Chem. Asian J. 2010, 5, 1120-1128
36. Resa, I.; Carmona, E.; Gutierrez-Puebla, E.; Monge, A. Science 2004, 305, 1136-1138
37. Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133-173
38. Negishi, E.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc. Chem. Res. 2008, 41, 1474-1485
39. Negishi, E. Angew. Chem., Int. Ed. 2011, 50, 6738-6764
40. Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154-5155
41. Takahashi, T.; Li, Y.; Stepnicka, P.; Kitamura, M.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 576-582
42. Huang, W.; Zhou, X.; Kanno, K.; Takahashi, T. Org. Lett. 2004, 6, 2429-2431
43. Seri, T.; Qu, H.; Zhou, L.; Kanno, K.; Takahashi, T. Chem. Asian J. 2008, 3, 388-392
44. Zhou, L.; Nakajima, K.; Kanno, K.; Takahashi, T. Tetrahedron Lett. 2009, 50, 2722-2726
45. Ni, Y.; Nakajima, K.; Kanno, K.; Takahashi, T. Org. Lett. 2009, 11, 3702-3705
46. Takahashi, T.; Sun, W.-H.; Xi, C.; Ubayama, H.; Xi, Z. Tetrahedron 1998, 54, 715-726